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Synthesis of New Cyclic Phosphate of Arylglyoxylonitrile Oximeand Their diastereomers

Chinese Chemical Letters 1999年第6期10卷 445-446页

作者： Zhi Hua MA Rut Lian SHAO Hong Min MA Jun Ran CHENG Run Qiu HUANG(National Key Laboratory of Elemento -Organic chemistry Nankai University. Tianjin 300071) Nankai Univ Natl Key Lab Elementoorgan Chem Tianjin 30071 Peoples R China

Keeping in view the biological activities of 1,3,2-dioxaphosphorinane-2-one and oxime esters. some compounds possessing these two moieties have been synthesized. The configurational assignment and the ratio of cis/trans diastereomers of target products were performed on basis of H-1 NMR. P-31 NMR and confirmed by X-ray diffraction analysis.

关键词： 1,3,2-dioxaphosphorinane-2-one arylglyoxylonitrile diastereomers

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Convenient synthesis of nucleoside 5'-(α-P-thio)triphosphates and phosphorothioate nucleic acids(DNA and RNA)

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Science China Chemistry 2012年第1期55卷 80-89页

作者： CATON-WILLIAMS Julianne FIAZ Bilal HOXHAJ Rudiona SMITH Matthew Department of Chemistry Georgia State University

Modified deoxy-and ribo-nucleoside triphosphates are chemically synthesized in multiple steps due to the protection and deprotection of the nucleoside *** conveniently synthesize the S-modified triphosphates for enzymatically preparing phosphorothioate DNAs and RNAs(PS-DNA and PS-RNA) as potential therapeutics,herein we report a one-pot strategy to synthesize the deoxy-and ribo-nucleoside 5'-(α-P-thio)triphosphates(dNTPαS and NTPαS) without protecting any nucleoside *** facile synthesis is achieved by treating the nucleosides with a mild phosphitylating reagent,reacting selectively with the 5'-hydroxyl group of each unprotected nucleoside,followed by sulfurization and hydrolysis to afford the crude dNTPαS and NTPαS analogs(mixtures of Sp and Rp diastereomers).We also demonstrated that after just simple precipitation(without HPLC and ion-exchange purification),the quality of the synthesized dNTPαS and NTPαS analogs is excellent for direct DNA polymerization and RNA transcription,*** Klenow DNA polymerase and T7 RNA polymerase accept the Sp diastereomers of dNTPαS and NTPαS analogs,respectively,while the Rp diastereomers are neither substrates nor inhibitors,the diastereomerically-pure PS-DNAs and PS-RNAs can be conveniently synthesized enzymatically.

关键词： sulfur modification S-derivatized nucleic acid nucleoside triphosphates nucleoside phosphorothioates phosphorothioate DNA and RNA diastereomers DNA and RNA polymerases

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Single-run reversed-phase HPLC method for determining sertraline content,enantiomeric purity,and related substances in drug substance and finished product

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Journal of Pharmaceutical Analysis 2020年第6期10卷 610-616页

作者： Alessia Rosetti Rosella Ferretti Leo Zanitti Adriano Casulli Claudio Villani Roberto Cirilli National Centre for the Control and Evaluation of Medicines Chemical Medicines UnitIstituto Superiore di Sanita(ISS)Viale Regina Elena 29900161RomeItaly Department of Chemistry and Technology of Drugs Sapienza University of Rome00185RomeItaly WHO Collaborating Centre for the Epidemiology Detection and Control of Cystic and Alveolar EchinococcosisEuropean Union Reference Laboratory for ParasitesIstituto Superiore di Sanita(ISS)Viale Regina Elena 29900161RomeItaly

A direct enantio-,diastereo-,and chemo-selective high-performance liquid chromatographic method was developed for determining the content,enantiomeric purity,and related substances of the chiral antidepressant drug sertraline HCl in a single chromatographic *** separation was achieved on a chiral stationary phase based on amylose tris(3-chloro-5-methylphenylcarbamate)under reversed-phase *** method was optimized by evaluating the influence of the temperature and mobile phase composition on the retention and *** application of the single-run approach allowed to baseline resolve all investigated species in less than 15 min,without using buffers or tandem-coupled *** chromatographic method was validated according to the guidelines of the Official Medicines Control Laboratory and applied to control the content of sertraline HCl and related chiral substances in a generic antidepressant formulation.

关键词： Chiralpak IG-3 Enantiomers diastereomers Reversed-phase enantioselective HPLC Sertraline HCl

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A Novel Approach for the Synthesis of (R) and (S)-Nicotine

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International Journal of Organic Chemistry 2022年第4期12卷 189-199页

作者： Rohith Kumar Agarthimoole Sahir Gagan Sudesna Parida Tarur Konikkaledom Dinesh Maheswaran S. Karatholuvhu Namasivayam Palani Soumitra Mukherjee ITC Limited ITC Life Sciences and Technology Centre Peenya Industrial Area Phase I Bangalore India Presently at Department of Atmospheric Sciences Texas A&M University College Station Texas USA

Nicotine is an alkaloid mainly found in leaves of tobacco and is used therapeutically for patients seeking relief from tobacco dependence in the form of products such as gums, patches, lozenges etc. In these products, majorly nicotine derived from tobacco is used which is inherently contaminated with undesirable nicotine related substances as impurities at low levels and is difficult to remove. Hence, use of synthetic nicotine is considered as an option which will be devoid of such impurities. In this work, a short and efficient synthesis of (R) and (S) nicotine was achieved by leveraging a key esterification between racemic homoallylic alcohol intermediate (2) and (S)-Ibuprofen (3) to produce diastereomers (5a) and (5b) which were easily separable under standard column chromatography conditions. Use of (S)-Ibuprofen (3) as a chiral resolving agent constitutes a novel approach which was not reported earlier. A subsequent hydrolysis of the diastereomers furnished the homoallylic alcohol intermediates (S)-6a and (R)-6a with high enantiopurity, which was effectively translated to the corresponding (R)-nicotine and (S)-nicotine respectively.

关键词： Nicotine Ibuprofen diastereomers Column Chromatography Chiral Purity

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